Highly functionalised (γ-azido/γ-fluoro-β-iodo/)vinyl derivatives from phosphorus based allenes or allenoates: I?O halogen bonding interactions?
Organic & Biomolecular Chemistry Pub Date: 2019-05-10 DOI: 10.1039/C9OB00715F
Abstract
Multifunctional γ-azido/γ-fluoro-β-iodo-vinyl phosphine oxides/phosphonates/esters/sulfone were synthesised by iodination followed by azidation/fluorination of phosphorus-based allenes or allenoates (allenyl esters) or a sulphur based allene. Surprisingly, the reaction of (γ,β)-diiodo-vinyl-phosphonate with TBAF [n-Bu4NF] led to the corresponding allenylphosphonate; in contrast, the use of CsF in a similar reaction led to novel γ-diiodo-allenylphosphonate along with the corresponding non-halogenated allenylphosphonate. The combination AgF2/CuBr could be used to obtain the γ-fluoro-β-iodo-vinyl phosphine oxides and related phosphorus-free γ-fluoro-β-iodo-vinyl esters. In many cases, I?O halogen to oxygen non-covalent bonding interactions (‘halogen bonding’) involving the phosphoryl (P![[double bond, length as m-dash]](https://www.rsc.org/images/entities/char_e001.gif)
O) oxygen, as evidenced by single crystal X-ray crystallography, are also observed.
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Journal Name：Organic & Biomolecular Chemistry
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CAS no.: 89640-58-4
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